WO2019056123A1 - Formulations topiques de cannabinoïdes et leur utilisation dans le traitement de la douleur - Google Patents

Formulations topiques de cannabinoïdes et leur utilisation dans le traitement de la douleur Download PDF

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Publication number
WO2019056123A1
WO2019056123A1 PCT/CA2018/051194 CA2018051194W WO2019056123A1 WO 2019056123 A1 WO2019056123 A1 WO 2019056123A1 CA 2018051194 W CA2018051194 W CA 2018051194W WO 2019056123 A1 WO2019056123 A1 WO 2019056123A1
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Prior art keywords
pharmaceutical composition
group
cannabinoid
therapeutically effective
cannabinoids
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Ceased
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PCT/CA2018/051194
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English (en)
Inventor
Hayes WONG
Sazzad HOSSAIN
Brian Cairns
Karen Ann LONG
Alexandra Mancini
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Inmed Pharmaceuticals Inc
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Inmed Pharmaceuticals Inc
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Priority to EP18859736.3A priority Critical patent/EP3684353A4/fr
Priority to US16/649,119 priority patent/US12357604B2/en
Publication of WO2019056123A1 publication Critical patent/WO2019056123A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/658—Medicinal preparations containing organic active ingredients o-phenolic cannabinoids, e.g. cannabidiol, cannabigerolic acid, cannabichromene or tetrahydrocannabinol
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0014—Skin, i.e. galenical aspects of topical compositions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/01—Hydrocarbons
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/045—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/075—Ethers or acetals
    • A61K31/08—Ethers or acetals acyclic, e.g. paraformaldehyde
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
    • A61K31/343—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide condensed with a carbocyclic ring, e.g. coumaran, bufuralol, befunolol, clobenfurol, amiodarone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/397—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having four-membered rings, e.g. azetidine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/415—1,2-Diazoles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/4164—1,3-Diazoles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/4164—1,3-Diazoles
    • A61K31/4178—1,3-Diazoles not condensed 1,3-diazoles and containing further heterocyclic rings, e.g. pilocarpine, nitrofurantoin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
    • A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/14—Esters of carboxylic acids, e.g. fatty acid monoglycerides, medium-chain triglycerides, parabens or PEG fatty acid esters
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/24—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing atoms other than carbon, hydrogen, oxygen, halogen, nitrogen or sulfur, e.g. cyclomethicone or phospholipids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/06—Ointments; Bases therefor; Other semi-solid forms, e.g. creams, sticks, gels
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/04—Centrally acting analgesics, e.g. opioids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings

Definitions

  • the method comprises peripherally (e.g., topically) administering a therapeutically effective quantity of a cannabinoid selected from the group consisting of rimonabant, JWH-018 (naphthalen-l-yl-(l-pentylindol-3- yl)methanone), JWH-073 naphthalen-l-yl-(l-butylindol-3-yl)methanone, CP-55940 (2- [(lR,2R,5R)-5-hydroxy-2-(3-hydroxypropyl) cyclohexyl]-5-(2-methyloctan-2-yl)phenol), dimethy lheptylpyran, HU-331 (3 -hy droxy-2- [( lR)-6-isopropenyl-3 -methy l-cyclohex-2-en- 1 - yl]-5-pentyl-l,4-benzoquinone),
  • the composition is a peripheral (e.g., topical) formulation containing a therapeutically effective quantity of one or more cannabinoids, wherein each of the one or more cannabinoids is independently selected from the group consisting of classical cannabinoids, endocannabinoids, non-classical cannabinoids, aminoalkylindoles and eicosanoids.
  • the composition comprises an additional therapeutically active agent selected from the group consisting of a topical anti-inflammatory agent, and a topical steroid. In some embodiments, the composition comprises a therapeutically effective quantity of a terpenoid.
  • Fig. 6 illustrates the mean ( ⁇ SE) mechanical withdrawal threshold of 6 female rats per treatment group following intramuscular injections of (A) THC (lmg/ml), (B) CBD (1 and 5mg/ml) and (C) CBN (lmg/ml), (D) CBC (lmg/ml) in behavioral experiments.
  • Significant differences were observed for THC, CBD (5mg/ml), and CBN compared to vehicle by 2-way repeated measures ANOVA. * indicates significant differences compared with the vehicle group and # indicates a significant difference compared to the NGF baseline within the treatment group (Holm Sidak multiple comparison test, p ⁇ 0.05).
  • a topical formulation refers to a pharmaceutical formulation suitable for topical administration.
  • exemplary embodiments include a cream or an aqueous or non-aqueous liquid formulation.
  • a peripheral formulation refers to a pharmaceutical formulation suitable for peripheral (e.g. , topical) administration.
  • Alkylene refers to a straight or branched, saturated, aliphatic radical having the number of carbon atoms indicated, and linking at least two other groups, i.e., a divalent hydrocarbon radical.
  • the two moieties linked to the alkylene can be linked to the same atom or different atoms of the alkylene group.
  • a straight chain alkylene can be the bivalent radical of -(CH 2 )n-, where n is 1 , 2, 3, 4, 5 or 6.
  • Representative alkylene groups include, but are not limited to, methylene, ethylene, propylene, isopropylene, butylene, isobutylene, sec-butylene, pentylene and hexylene.
  • Alkylene groups can be substituted or unsubstituted.
  • Alkenylene refers to an alkenyl group, as defined above, linking at least two other groups, i.e., a divalent hydrocarbon radical.
  • the two moieties linked to the alkenylene can be linked to the same atom or different atoms of the alkenylene.
  • Alkenylene groups include, but are not limited to, ethenylene, propenylene, isopropenylene, butenylene, isobutenylene, sec-butenylene, pentenylene and hexenylene.
  • Alkenylen groups can be substituted or unsubstituted.
  • heterocycloalkyl groups can also be fused to aromatic or non-aromatic ring systems to form members including, but not limited to, indoline.
  • Heterocycloalkyl groups can be unsubstituted or substituted.
  • Heteroaryl groups can have from 5 to 8 ring members and from 1 to 4 heteroatoms, or from 5 to 8 ring members and from 1 to 3 heteroatoms, or from 5 to 6 ring members and from 1 to 4 heteroatoms, or from 5 to 6 ring members and from 1 to 3 heteroatoms.
  • the heteroaryl group can include groups such as pyrrole, pyridine, imidazole, pyrazole, triazole, tetrazole, pyrazine, pyrimidine, pyridazine, triazine (1,2,3-, 1,2,4- and 1,3,5-isomers), thiophene, furan, thiazole, isothiazole, oxazole, and isoxazole.
  • heteroatom refers to any atom that is not carbon or hydrogen, such as nitrogen, oxygen or sulfur. When it is part of the backbone or skeleton of a chain or ring, a heteroatom must be at least divalent, and will typically be selected from N, O, P, and S.
  • the compounds described herein may contain one or more chiral centers and/or double bonds and therefore, may exist as stereoisomers, such as double-bond isomers (i.e., geometric isomers such as E and Z), enantiomers or diastereomers.
  • stereoisomers such as double-bond isomers (i.e., geometric isomers such as E and Z), enantiomers or diastereomers.
  • the invention includes each of the isolated stereoisomeric forms (such as the enantiomerically pure isomers, the E and Z isomers, and other alternatives for stereoisomers) as well as mixtures of stereoisomers in varying degrees of chiral purity or percentage of E and Z, including racemic mixtures, mixtures of diastereomers, and mixtures of E and Z isomers.
  • protecting groups can be included in compounds used in methods according to the present invention or in compositions according to the present invention.
  • the use of such a protecting group is to prevent subsequent hydrolysis or other reactions that can occur in vivo and can degrade the compound.
  • Groups that can be protected include alcohols, amines, carbonyls, carboxylic acids, phosphates, and terminal alkynes.
  • prodrug refers to a precursor compound that, following administration, releases the biologically active compound in vivo via some chemical or physiological process ⁇ e.g., a prodrug on reaching physiological pH or through enzyme action is converted to the biologically active compound).
  • a prodrug itself may either lack or possess the desired biological activity.
  • prodrug refers to a precursor of a biologically active compound that is pharmaceutically acceptable, n certain cases, a prodrug has improved physical and/or delivery properties over a parent compound from which the prodrug has been derived.
  • the prodrug often offers advantages of solubility, tissue compatibility, or delayed release in a mammalian organism (H.
  • CBN canbinol
  • the therapeutically effective composition contains a cannabinoid or a mixture of cannabinoids.
  • the composition contains cannabinol, optionally in combination with the cannabidiol ⁇ 2 -cannabidiol.
  • the mixture of cannabinoids is a mixture of cannabidiols selected from the group consisting of one or more of the cannabidiols described herein and cannabinol.
  • the ratio of the one or more cannabidiols (CBD) to cannabinol (CBN) is from 10:0.1 ⁇ g/mL to 0.1 : 10 ⁇ g/mL.
  • the cannabinoid can be an endocannabinoid or a derivative or analog thereof.
  • Endocannabinoids include but are not limited to anandamide, 2- arachidonoylglycerol, 2-arachidonyl glyceryl ether, N-arachidonoyl dopamine, and virodhamine.
  • a number of analogs of endocannabinoids are known, including 7,10,13,16- docosatetraenoylethanolamide, oleamide, stearoylethanolamide, and homo- ⁇ - linolenoylethanolamine, are also known.
  • the cannabinoids, or one of the cannabinoids in a mixture of cannabinoids is an inverse agonist (e.g., selective or non-selective inverse agonist) of CB1.
  • the cannabinoids, or one of the cannabinoids in a mixture of cannabinoids is a neutral antagonist (e.g., selective or non-selective neutral antagonist) of CB1.
  • the cannabinoids, or one of the cannabinoids in a mixture of cannabinoids is a partial agonist (e.g., selective or non-selective neutral agonist) of CB1.
  • the pharmaceutical composition comprises a mixture of two cannabinoids at a total cannabinoid concentration as described in one of the foregoing concentrations or concentration ranges and at a ratio of from (1 :0.1) to (0.1 : 1), from (1 :5) to (5: 1), or at a ratio of 1 : 1, 1 :2, 1 :5, 1 : 10, 1 : 15, 1 :20, 1 :25, 1 :50, 1 :75, or 1 : 100.
  • the foregoing ratios refer to a ratio of cannabidiols: cannabinol.
  • the foregoing ratios refer to a ratio of cannabinol: cannabidiols.
  • compositions including one or more excipients as described above.
  • Trigeminal ganglia and masseter muscles were removed, incubated in 20% and then 40% sucrose for 48h each to cryoprotect the tissue, and cut into 10 ⁇ sections with a cryotome.
  • Trigeminal ganglia sections were treated with 5% normal goat serum (NGS) in PBS for 1 h and incubated overnight with commercially available primary antibodies against CB1 (Santa Cruz Biotechnology, Dallas Texas) and CB2 receptors (ABCAM, Cambridge MA), TRPV1 channels (ABCAM, Cambridge MA). Satellite glial cells were identified by primary antibody against glutamine synthetase (GS; ABCAM, Cambridge MA).
  • Rats were anesthetized with isoflurane (2-2.5% in oxygen 97-98%; AErrane; Baxter) and surgically prepared for electrophysiological recording. Heart rate, blood pressure and body temperature were monitored and a trachea tube was inserted for ventilation throughout the experiment. The hair of the face was shaved and the animal's head was positioned in a stereotaxic frame. A diagram of the experimental setup is shown in Fig. 1.
  • Cannabinoids attenuate capsaicin-evoked hyperalgesia through spinal and peripheral mechanisms. Pain 2001;93:303-15.

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  • Chemical & Material Sciences (AREA)
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  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
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  • Oil, Petroleum & Natural Gas (AREA)
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  • Molecular Biology (AREA)
  • Pain & Pain Management (AREA)
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  • Neurosurgery (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Organic Chemistry (AREA)
  • Dermatology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

L'invention concerne des compositions pharmaceutiques comprenant un ou plusieurs cannabinoïdes et un vecteur pharmaceutiquement acceptable. Les compositions se présentent sous une forme convenant à une administration topique, et peuvent servir à traiter la douleur. Les cannabinoïdes qui conviennent à cette utilisation comprennent des cannabidiols, des cannabinols, et divers autres cannabinoïdes naturels et synthétiques. Les compositions peuvent également comprendre en outre des agents anti-inflammatoires, des stéroïdes, ou des terpénoïdes. Selon des modes de réalisation préférés, les cannabinoïdes incorporés dans les compositions sont le cannabidiol (CBD) et le cannabinol (CBN), et les vecteurs sont sélectionnés dans le groupe constitué par le Labrasol™, le Transcutol™, la lécithine, la lysolécithine, le palmitate d'isopropyle et le myristate d'isopropyle.
PCT/CA2018/051194 2017-09-22 2018-09-21 Formulations topiques de cannabinoïdes et leur utilisation dans le traitement de la douleur Ceased WO2019056123A1 (fr)

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EP18859736.3A EP3684353A4 (fr) 2017-09-22 2018-09-21 Formulations topiques de cannabinoïdes et leur utilisation dans le traitement de la douleur
US16/649,119 US12357604B2 (en) 2017-09-22 2018-09-21 Topical formulations of cannabinoids and use thereof in the treatment of pain

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US201762562166P 2017-09-22 2017-09-22
US62/562,166 2017-09-22

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Cited By (15)

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WO2020163866A1 (fr) * 2019-02-08 2020-08-13 Schedule 1 Therapeutics, Inc. Compositions comprenant des cannabinoïdes et leurs procédés d'utilisation
WO2021030190A1 (fr) * 2019-08-09 2021-02-18 Jupiter Wellness, Inc. Formulations de cbd et leurs utilisations
CN113440508A (zh) * 2021-07-27 2021-09-28 昆明理工大学 大麻二酚衍生物的新应用
WO2021214545A1 (fr) * 2020-04-20 2021-10-28 Pike Therapeutics, Inc. Formulations pharmaceutiques transdermiques et/ou topiques comprenant du cannabidiol et/ou du tétrahydrocannabinol pour le traitement de la douleur chronique
US11160768B2 (en) 2019-10-22 2021-11-02 Edmund M. Dunn Paraffin wax with CBD isolate
WO2021243201A1 (fr) * 2020-05-29 2021-12-02 The University Of Mississippi Compositions topiques pour le traitement de la douleur neuropathique périphérique
WO2022008955A1 (fr) 2020-07-08 2022-01-13 Herba Invest, Pte. Ltd. Préparations contenant un extrait de mitragynine ou ses alcaloïdes isolés et un extrait de cannabis ou ses cannabinoïdes isolés, et utilisation cosmétique et/ou pharmaceutique de celles-ci
CN114096671A (zh) * 2019-03-06 2022-02-25 因美制药公司 用于在异源系统中生物合成类萜或大麻素的组合物和方法
WO2022219468A1 (fr) * 2021-04-12 2022-10-20 Pike Therapeutics, Inc. 1219014 B.C. Ltd. Administration transdermique de cannabidiol
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US20200289458A1 (en) 2020-09-17

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